Sally-Ann O’Callaghan. Image: Maxio
Maxio’s Sally-Ann O’Callaghan discusses standing out in the world of SaaS and how she took a transatlantic risk to get into tech.
Sally-Ann O’Callaghan became the new EMEA director for Chargify earlier this year. This US company, which develops a billing and subscription management platform for SaaS businesses, opened its EMEA headquarters in Dublin in 2020.
Last year, Battery Ventures invested $150m in Chargify and another business, SaaSOptics, with a view to merging the two. It was recently announced that the companies are coming together as one revenue management business under the brand Maxio.
Before joining the company, O’Callaghan spent nearly five years working across EMEA business development and sales acquisition roles at Dropbox. She will now oversee Maxio’s EMEA go-to-market operations out of its Dublin office and work to further scale the company’s growth in the region.
‘Getting in front of CEOs, CTOs and other decision-makers and having them prioritise one technology over others can be challenging’
– SALLY-ANN O’CALLAGHAN
What are the biggest challenges facing your sector and how are you tackling them?
Competition. And I don’t mean in the billing and finance operations market, I mean technology in general.
Getting in front of CEOs, CTOs and other decision-makers and having them prioritise one technology over others can be challenging. There are so many SaaS solutions in the market now – everything is very specialised.
For me, it’s about understanding what the customer needs and what’s important to them on a day-to-day basis so that I can understand how important what we’re offering to them is and how they will prioritise it.
I’m a big believer of investing in the right systems for growth for wherever you may be on the maturity curve, and then ensuring that our solution can be easily integrated into a client’s existing tech stack so that data is flowing seamlessly between all of their tools.
What are the key sector opportunities you’re capitalising on?
At Maxio, we see financial operations (FinOps) as a critical part of a SaaS company’s core competencies – just as important, in its own way, as building amazing products and a great brand.
Subscription-based SaaS businesses need a platform that provides the robust and flexible infrastructure and actionable intelligence needed to drive the business forward – regardless of whether you’re working with a partner or handling FinOps in-house with a homegrown system.
There are a lot of tools in the market that are really great for managing your subscription billing or either really strong at running your financial operations, but there wasn’t one that could provide both solutions – and do it well.
This is the market opportunity we’re capitalising on and why we’ve recently brought together two companies to create the new Maxio brand — Chargify, the leader in billing and subscription management for B2B SaaS, and SaaSOptics, which streamlines financial operations and provides powerful analytics.
We’re forging a new path forward for SaaS businesses and providing an all-in-one revenue management and advanced subscription billing solution for high-growth SaaS companies.
What set you on the road to where you are now?
I have a great support network through friends, family and professional peers and mentors from whom I always ask for help and advice.
I also tend to make decisions by gut feeling. Knowing when to trust my gut and go for it and when to ask others and look for help has really helped me get where I am.
What’s the biggest risk you’ve ever taken?
I moved to San Francisco on my own in 2015 to pursue a career in the technology industry. I had a steady job in Aviva in Ireland, which I really enjoyed, but I was really eager to get involved in the technology scene.
It was really only starting in Dublin and after applying to a few roles here and having no luck, I decided to chance my arm and head to the heart of it all in Silicon Valley.
This proved to be one of my best career moves to date as, after a lot of hard work, I landed myself a role in what was then the fastest-growing SaaS company ever.
What one work skill do you wish you had?
I would love to be multilingual. Being able to communicate with those in different countries, particularly in EMEA, would be very powerful.
How do you get the best out of your team?
I try to understand what motivates and drives them, what they care about and what makes them tick. Each member of the team is very unique so this helps me understand what matters to them and get the best from each individual.
Have you noticed a diversity problem in your sector?
Historically, I think there was always a diversity problem within the technology industry.
While I don’t believe the problem has been solved, I think we are moving in the right direction and truly believe there is a place for everyone in the industry. But we still have a lot of work left to do!
What books have you read that you would recommend?
We have a book club at Maxio and we recently read and discussed Measure What Matters by John Doerr. It was a really interesting and thought-provoking take on the importance of objectives and key results (OKRs) in business and in life.
For my own personal reading, I’ve read lots of great sales books that have stuck with me including Influence: The Psychology of Persuasion by Robert Cialdini and Never Split the Difference by Chris Voss.
What are the essential tools and resources that get you through the working week?
Coffee!
I’m pretty basic when it comes to tools and resources. I generally try to limit the amount of distractions by allotting time-based activities and using one single tracking doc. I currently use Google Drive all the time. At Dropbox, however, I was a heavy paper user, which was amazing for tracking my personal day-to-day activities.
For me, it’s not really about tools but about setting clear objectives for the day and sticking to tasks.
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